In November 2008, Barack Hussein Obama II was elected forty-fourth President of the United States. Caroline Kennedy felt strongly that Ted’s and her endorsement of him went a long way toward getting him in office; the family was both proud and happy, even those who had opposed his presidency. At least a Democrat had won.
On December 3, Caroline telephoned New York’s governor, David Paterson, to tell him of her intentions to be considered as a candidate for Hillary Clinton’s Senate seat. He wasn’t thrilled. It sounded like a stunt to him. Though Paterson would eventually need to appoint someone to that senatorial seat, he felt that Caroline just wanted it if it could be handed to her, which, in his mind, wasn’t fair to those he felt really deserved it—contenders like her cousin by marriage Andrew Cuomo, married to Kerry, a seasoned politician who had been an attorney general, a cabinet secretary, and a governor’s adviser. Also, in two years, Caroline would have to actually run in an election for that seat if she was now appointed to it, and Paterson didn’t think she would have it in her to wage a full-out campaign.
Still, she was Caroline Kennedy, so he wasn’t going to be completely dismissive of her. He told her to talk to people in local office, maybe go visit the mayor of New York City and other elected officials. He also suggested a tour of New York to put herself in public view. He hastened to add that she should stay away from answering too many questions from the media. That’s where he felt she would be at her most vulnerable.
As soon as Caroline made that call to Paterson, the story was leaked. Before she knew it, she had to mobilize a staff of advisers because people were now asking questions, they were getting excited, and her new interest in politics had become headline news overnight. As the frenzy continued to build, Caroline did the exact opposite of what most politicians might do under such circumstances. Instead of capitalizing on the moment, she retreated from it.
A good example: On December 5, Caroline attended a birthday party for a friend. After years of doing so, Caroline knew how to read a room. She could scope out a party and, as if she had some sort of radar, immediately figure out who she thought was an enemy, or at the very least, a skeptic. On this night, she sensed everyone as being against her. The subject of her running for Senate came up, of course. Rather than talk about a possible platform, she clammed up as if she were being asked a personal question about one of her kids or, worse yet, one of her parents. Such reticence wasn’t a good sign. Politicians who have fire in their bellies love to talk policy any chance they get, and that didn’t seem to be Caroline.
Despite any misgivings building within her, the groundswell for her possible campaign continued to mount. New York’s Mayor Michael Bloomberg even told the press it was a fait accompli that Caroline would run, and that people should just begin to get used to the idea. However, local politicians, like Gary Ackerman of New York’s Fifth District, disagreed. “One of the things we have to observe is that DNA in this business can take you just so far,” he said on television’s Face the Nation. “You know, Rembrandt was a great artist. His brother, Murray, on the other hand—well, Murray Rembrandt couldn’t paint a house.”
Very quickly, the knives came out for Caroline among more than a few Democrats who felt that they, not she, were better suited. New York politicians such as Carolyn Maloney, Steve Israel, and Tom Suozzi began to weigh in, but in subtle ways. They didn’t speak negatively about Caroline, but their surrogates spread the word that she was deeply unqualified. Governor Paterson, meanwhile, made it clear he wouldn’t support anyone, even Caroline, until after Hillary Clinton was officially confirmed as Secretary of State. It would be all about whoever could galvanize the most attention as a possible candidate.
Despite skepticism, after just a couple of weeks, by the middle of December, it appeared that people might actually accept Caroline Kennedy as a senator; in one poll, voters preferred her to Andrew Cuomo 33 percent to 29 percent. However, on the seventeenth when Caroline was asked during an impromptu interview exactly why she wanted to be a senator, she balked and didn’t seem to have an answer. Her aides rushed her from the room, which was duly reported by the press the next day.
That same week, Caroline went on to Rochester and Buffalo to give it her best shot in another interview, but something was definitely off. She was so ill at ease, it looked as if she was hiding something. Of course, the only thing she was trying to hide was just how much she hated answering questions.
“Whereas she was used to being on a pedestal, now she was always being shouted and screamed at,” observed her uncle Jamie Auchincloss. “She was naturally taken aback to be thrust into this carnival atmosphere. When she got out of Manhattan and got to know the folks in Rochester, Albany—the union halls and the PTAs—she realized how insulating her fame had been. Instead of cocktails in the homes of the top Democratic influencers in those areas as she may have expected, she was really in the trenches with the people … in hotels with hallways blocked off and amid heavy security as photographers climbed up the sides of walls and sneaked in windows. Advance men for her looked more like a presidential detail than the team of a state’s senatorial race. Because of all the security, she didn’t get to have those conversations with the people that were so necessary. Ultimately, she looked like a product instead of a person.”
The next week or so found Caroline dodging questions while her camp issued carefully written answers to media inquiries. Meanwhile, she spent her time boning up on policy. It had quickly become a real pressure cooker for her as she struggled with learning all there was to know in crash courses about New York politics, immigration, the economy, gay rights, and whatever her strategists felt she could handle. She began to realize that she was in over her head, as did everyone around her. However, she wasn’t raised to be a quitter; therefore, she would persevere. “We’re in the business of politics,” she knew her grandfather used to say. “We’re not here to lose. We’re here to win.”
On December 26, Caroline gave an interview to the Associated Press and managed to get through it, as well as a TV interview with NY1’s Inside City Hall. She went home that night feeling that maybe she’d done a fairly decent job in addressing immigration and education concerns. Some were impressed. “You always get a sense of entitlement or a sense of royalty, whether it’s the Rockefellers or the Kennedys, and she never came off like that,” said Al Sharpton, who had a lunch with her in Harlem. “It was never like she felt like you were honored to meet her. She came off very studious, very sober, very serious. And I had that impression of her way before she ever thought about politics.”
The next morning, though, things began to deteriorate when Caroline sat down with reporters Nicholas Confessore and David M. Halbfinger from The New York Times. They didn’t want to know her position on policy as much as they wanted a clear-cut answer, once and for all, to a simple question: Why did she want to be a senator? Her simple interest in the job wasn’t enough for her to deserve it. What was her motivation? What would be her platform? She was now being asked basically the same obvious question that had ruined her uncle’s chances almost thirty years earlier when he didn’t know how to explain his desire to be President.
The question as to why a person wants to lead is not a difficult one if that person has deeply considered and held ideals and beliefs. It can and should be answered with strength, clarity, and determination. However, if a person is unsure or even faking it, things can take a dramatic turn for the worst—which is what happened with Ted and what now happened to Caroline. She gave a weak response rife with “you knows” and “ums.” As was later oft-reported, she said “you know” almost two hundred times in the course of about an hour:
I think that what we’ve seen over the last year, and particularly and even up to the last—is that there’s a lot of different ways that people are coming into public life now, and it’s not only the traditional path. Even in the New York delegation, you know, some of our great senators—Hillary Clinton, Pat Moynihan—came from, you know, other walks of life. So, I don’t think that that is, uh—so I think in many ways, you know, we want to have all kinds of different voices, you know, representing us, and I think what I bring to it is, you know, my experiences as a mother, as a woman, as a lawyer, you know, I’ve been an education activist for the last six years and, you know, I’ve written seven books—two on the Constitution and two on American politics. So, obviously, you know …
When asked why she hadn’t given Hillary Clinton an earlier heads-up when she planned to support Barack Obama, Caroline became flustered and refused to answer.
I think this is about the future, and, um, you know, that’s what I want to talk about, which is, what’s going on in our state, you know, why I would be the best person to help deliver for New York. We’re facing, you know, an economic crisis, the paper this morning said there’s, you know, five billion dollars of construction projects which just stopped, you know, that’s, you know—conversations a year ago, that—besides, that, I don’t, as I said, I have conversations with a lot of people, and those are confidential.
None of what she said made Caroline sound particularly articulate or informed, which was a shame because she had a better grasp of the issues than her rambling monologue would suggest. The problem for Caroline wasn’t a lack of knowledge as much as it was an inability to convey it effectively. Like a lot of politicians, she was better with practiced talking points than she was with shooting from the hip.
Things got even worse when, in an effort to try to get Caroline to recount what happened when she told Ed that she wanted to be a senator, the reporters asked, “for the sake of storytelling, could you tell us a little about that moment?” Her answer? “Have you guys ever thought about writing for, like, a woman’s magazine, or something?” Of course, the next question was, “What do you have against women’s magazines?” She snapped back, “Nothing at all, but I thought you were the crack political team here.”
Apparently, the final straw for Caroline came when the writers pushed her about how much she lived on a year: “Is it $2 million? Is it less than $2 million? Is it more than $5 million?” Now she was really peeved, and she couldn’t hide it; she refused to answer.
“If I can just throw one more question out there,” David Halbfinger suggested.
“I think we’re done,” Caroline announced.
When the article was published on December 27, 2008, it was devastating. Unfortunately, the publication’s editors opted not only for a feature but also a word-by-word transcript in which they published every “you know” and every “um” she’d muttered. It made her appear to be inarticulate. It probably never would have happened, though, if she had not insulted the writers. She was hurt, embarrassed, and, ultimately, outraged.
“They made me look like a complete idiot,” she raged to one member of her campaign staff. She took the newspaper, rolled it up, and slapped it hard on a desk. “See? This is why I don’t give interviews,” she said angrily. “These jerks knifed me right in the back.” This kind of emotional display was unusual for Caroline; she’d never been an emotive person. It looked to some as if the stress of the last couple of weeks was really getting to her. She also blamed the PR company she had hired to roll out her campaign; clearly, in her mind at least, its publicists had totally miscalculated her preparation—or lack thereof—for such an important interview.
“She’s not glib in the way that predictable politicians are glib,” Richard Plepler, who was a copresident at HBO and a friend of Caroline’s, noted after the article was published. “She is thoughtful, articulate, and fundamentally decent, and if you discussed any number of complicated issues with her that are currently part of the political dialogue, she would be both informed and deeply thoughtful.”
Plepler’s particular view of Caroline didn’t appear to be borne out by her many stammering responses to questions from those New York Times reporters. History shows that this particular interview Caroline Kennedy gave to the so-called Old Gray Lady pretty much marked the end of the line for her.